Methyl iodide → 4-(2-ethoxy-2-oxoethyl)-1,1-dimethyl-4-(N-(4-octylphenyl)sulfamoyl-amino)piperidinium iodide
Reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])([NH:8][S:9](=[O:26])(=[O:25])[NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:13][CH:12]=2)[CH2:4][CH2:3]1.[CH3:33][I:34]>>[I-:34].[CH2:31]([O:30][C:28](=[O:29])[CH2:27][C:5]1([NH:8][S:9](=[O:25])(=[O:26])[NH:10][C:11]2[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:15][CH:16]=2)[CH2:6][CH2:7][N+:2]([CH3:33])([CH3:1])[CH2:3][CH2:4]1)[CH3:32]Participants
Procedure
Ethyl 2-(1-methyl-4-(N-(4-octylphenyl)sulfamoylamino)piperidin-4-yl)acetate (39 mg, 0.084 mmol), was treated with MeI (0.2 mL, 3.2 mmol) as described in example 2a to yield crude 4-(2-ethoxy-2-oxoethyl)-1,1-dimethyl-4-(N-(4-octylphenyl)sulfamoyl-amino)piperidinium iodide which was used without further purification. Subsequent saponification and preparative HPLC purification gave the title compound (8 mg, 17%) as white solid. 1H NMR (400 MHz, CD3OD) δ 7.20 (d, 2H, J=8.4 Hz), 7.15 (d, 2H, J=8.8 Hz), 3.27-3.15 (m, 4H), 3.08 (s, 3H), 2.88 (s, 2H), 2.81 (s, 3H), 2.59 (t, 2H, J=15.6 Hz), 2.39 (d, 2H, J=15.6 Hz), 2.26-2.18 (m, 2H), 1.65-1.55 (m, 2H), 1.48-1.25 (m, 10H), 0.91 (t, 3H, J=6.8 Hz); MS ESI 454.3 [M+H]+, calcd for [C23H39N3O4S+H]+ 454.27.
Sources & evidence
- ORD record
- ord-bff7ab459e1d4ae3af87111fb158d270
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680282B2
Reaction notes
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